Unexpected switch in regioselectivity of tether-directed Bingel-type biscyclopropanations depending on the leaving groups at tethered active methylene moieties‡
Literature Information
Tetsuo Hino, Kazuhiko Saigo
The regioselectivity of tether-directed Bingel-type biscyclopropanations of [60]fullerene was switched depending on the leaving groups at tethered active methylene moieties; the reactions of [60]fullerene with unhalogenated tethered bis(active methylene) derivatives/I2 and with brominated derivatives in the presence of 1,7-diazabicyclo[5.4.0]undec-7-ene gave trans-4-adducts predominantly, while the reactions with chlorinated derivatives afforded equatorial-adducts almost exclusively.
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![5,10-Dihydroindeno[2,1-a]indene structure 5,10-Dihydroindeno[2,1-a]indene structure](https://static.chemtradehub.com/structs/654/6543-29-9-71ca.webp)

![Ethyl 4-[8-chloro(5,5,6,6,7-~2~H_5_)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene]-1-piperidinecarboxylate structure Ethyl 4-[8-chloro(5,5,6,6,7-~2~H_5_)-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene]-1-piperidinecarboxylate structure](https://static.chemtradehub.com/structs/102/1020719-57-6-37e2.webp)
